Autori su u svrhu što boljeg upoznavanja s problematikom teme metodom slučajnog odabira pregledali predmete iz novoosnovanog upisnika I Kž-uv Visokog kaznenog suda Republike Hrvatske od početka rada 1. siječnja 2021. pa zaključno s 31. prosinca 2023., dakle za prve tri godine rada toga suda, a u povodu žalbe protiv rješenja prvostupanjskih sudova kojima se odobrava ili odbija prijedlog zatvorenika (ranije i kaznionice) za uvjetni otpust. Predmeti su analizirani s pozicija ispunjenja zakonskih uvjeta za odobravanje uvjetnog otpusta u smislu članka 59. KZ/11, i to kroz omjer izdržanog i neizdržanog dijela kazne zatvora u slučaju odobravanja uvjetnog otpusta u vezi sa zakonom propisanim minimumom od najmanje polovine kazne na koju je zatvorenik osuđen, ali ne manje od tri mjeseca. Nadalje, pri analizi predmeta razmotrene su okolnosti iz članka 59. stavka 2. KZ/11 kojima se sud rukovodi prilikom odlučivanja o prijedlogu za uvjetni otpust, a koje se utvrđuju na temelju izvješća kaznionice odnosno zatvora u kojem zatvorenik izdržava kaznu. Izvješće sadrži i mišljenje kaznionice o prijedlogu za uvjetni otpust kao obvezni element koji se razmatra te izvješća probacijskog ureda i dostupne podatke zavoda za socijalnu skrb kao fakultativne elemente u korelaciji s osnovnim ciljem kojim se sud rukovodi, a to je utemeljeno očekivanje da zatvorenik neće počiniti novo kazneno djelo, koje je dijagnostičke naravi. Kroz pregled sudske prakse autori su pokušali dati odgovore na praktične dileme koje su se pojavile prilikom odlučivanja u žalbenom postupku, kao i istaknute normativne nedostatke koji prate Zakon o izvršavanju kazne zatvora iz 2021., prvenstveno u pogledu ovlaštenika za podnošenje prijedloga za uvjetni otpust i žalbe na prvostupanjsko rješenje, kao i dati odgovor na pitanje je li novo uređenje instituta uvjetnog otpusta tegobnije za zatvorenike i kakve konzekvence ono izaziva.In order to better familiarise themselves with the issue of this topic, the authors reviewed cases from the newly established Register I Kž-uv of the High Criminal Court of the Republic of Croatia from the beginning of work on 1 January 2021 and ending on 31 December 2023, hence for the first three years’ work of that court, using a random selection method in the context of appeals against the decisions of first-instance courts approving or rejecting the prisoner’s (previously also the penitentiary’s) proposal for conditional release. The cases were analysed from the standpoint of fulfilling the legal conditions for granting conditional release in the sense of Article 59 of the Criminal Code/11 and through the ratio of the served and unserved part of the prison sentence in the case of granting conditional release in connection with the legally prescribed minimum of at least half of the sentence to which the prisoner was sentenced, but not less than three months. Furthermore, when analysing the case, the circumstances under Article 59, paragraph 2 CC/11 were considered which the court is guided by when deciding on a proposal for conditional release, circumstances which are determined on the basis of a report of the penitentiary or the prison where the prisoner is serving his sentence. Such considerations also contains the opinion of the penitentiary on the proposal for conditional release as a mandatory element to be taken into account, and the reports of the probation office and the available data of the institutions for social welfare as optional elements in correlation with the basic goal that the court is guided by, which is the well-founded expectation that the prisoner will not commit a new criminal offence, which is of a diagnostic nature. Through a review of judicial practice, the authors attempt to provide answers to the practical dilemmas that arise when deciding in the appeal procedure, as well as regarding the highlighted normative shortcomings that accompanied the “new” Act on the Execution of Prison Sentences of 2021, primarily with regard to the authorised persons for submitting proposals for conditional release and appeals against the first-instance decision. The authors also attempt to provide an answer to the question of whether the new arrangement of conditional release is more difficult for prisoners and consider what consequences this may cause